US3803085A - Method for making polyetherimides - Google Patents

Method for making polyetherimides Download PDF

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US3803085A
US3803085A US00319372A US31937272A US3803085A US 3803085 A US3803085 A US 3803085A US 00319372 A US00319372 A US 00319372A US 31937272 A US31937272 A US 31937272A US 3803085 A US3803085 A US 3803085A
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bis
parts
dicarboxyphenoxy
polymer
dianhydride
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US00319372A
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T Takehoshi
J Kochanowski
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General Electric Co
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General Electric Co
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Priority to US00319372A priority Critical patent/US3803085A/en
Priority to US00372743A priority patent/US3833546A/en
Priority to GB5935673A priority patent/GB1463299A/en
Priority to DE2363784A priority patent/DE2363784C2/de
Priority to CA188,947A priority patent/CA1013492A/en
Priority to JP744918A priority patent/JPS5720967B2/ja
Priority to IT32186/73A priority patent/IT1002289B/it
Priority to FR7347097A priority patent/FR2225466B1/fr
Priority to US05/439,866 priority patent/US3989670A/en
Application granted granted Critical
Publication of US3803085A publication Critical patent/US3803085A/en
Priority to FR7428600A priority patent/FR2225470B1/fr
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1042—Copolyimides derived from at least two different tetracarboxylic compounds or two different diamino compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1003—Preparatory processes
    • C08G73/1007—Preparatory processes from tetracarboxylic acids or derivatives and diamines
    • C08G73/1028—Preparatory processes from tetracarboxylic acids or derivatives and diamines characterised by the process itself, e.g. steps, continuous
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1046—Polyimides containing oxygen in the form of ether bonds in the main chain
    • C08G73/1053—Polyimides containing oxygen in the form of ether bonds in the main chain with oxygen only in the tetracarboxylic moiety
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1057—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain
    • C08G73/106—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain containing silicon

Definitions

  • the present invention relates to a melt polymerization process for making polyetherimides based on the reaction between certain aromatic bis(etheranhydride)s and organic diamines.
  • polyimides Prior to the present invention polyimides were generally made from a polyarnide acid intermediate. A dipolar aprotic solvent is required to produce such polyamide acid intermediate before it can be converted to the polyimide state. Unlike polyamides, polyimides are intractable and decompose before they can be melted. At best, the more readily processable polyamide acid can be converted to a film or coating. However, the removal of solvent causes air pollution.
  • polyetherimide reaction products of aromatic bis(etheranhydride) and organic diamine can be made at elevated temperatures in the presence of organic solvent to produce moldable polyehterimides.
  • organic solvent is required which causes air pollution.
  • several additional processing steps are necessary before the final product can be recovered.
  • the present invention is based on the discovery that moldable polyetherimides can be made directly from certain aromatic bis(etheranhydride)s and organic diamines, as defined hereinafter, in the absence of organic solvent. These polyetherimide forming ingredients can be melt polymerized at temperatures up to 350 C.
  • a method for making polyetherimides which comprises eifecting the removal of water of reaction at temperatures up to 350 C. from the melt of a mixture containing as essential ingredients aromatic bis(etheranhydride) of the and organic diamine of the formula, (2) H NR NH where R is a divalent aromatic organic radical having from 6-30 carbon atoms, R is a divalent organic radical selected from R radicals, alkylene radicals having from 2-20 carbon atoms, cycloalkylene radicals, and C(24) alkylene terminated polydiorganosiloxane radicals.
  • Radicals included by R are, for example, aromatic hydrocarbon radicals and halogenated aromatic hydrocarbon radicals, for example, phenylene, tolylene, chloro- 3,803,085v Patented Apr. 9, 1974 Too phenylene, naphthalene, etc., and radicals included by the formula,
  • R is a divalent aromatic radical having from 6-13 carbon atoms selected from hydrocarbon radicals and halogenated hydrocarbon radicals
  • Q is a divalent organo radical selected from where a is 0 or 1
  • y is an integer having a value of from 1-5 inclusive
  • R is a monovalent hydrocarbon radical selected from methyl, phenyl, etc.
  • Radicals included by R are, for example,
  • alkylene radicals such as hexamethylene, etc., cyclohexylene, etc.
  • Dianhydrides included by Formulas 4 and 5 are for example,
  • aromatic bis(etheranhydride)s also included by Formula 1 are shown by Koton, M. M.; Florinski, F. S.; M. L; Rudakov, A. T. (Institute of Heteroorganic Compounds, Academy of Sciences, U.S.S.R.) U.S.S.R. 257,010, 11 November 1969, APPL 03 May 1967.
  • dianhydrides shown M. M. Koton, F. S. Florinski, Zh Org. Khin 4(5) 774 (1968).
  • aromatic bis(etheranhydrides) of Formula 1 are shown in copending application of Darrell Heath and Joseph Wirth Ser. No. 281,749, filed Aug. 18, 1972, and assigned to the same assignee as the present inven tion.
  • These dianhydrides can be prepared from the hydrolysis, followed by dehydration of the reaction product of a nitro-substituted phenyl dinitrile with a metal salt of a dihydric phenol compound in the presence of a dipolar aprotic solvent.
  • a benzenoid compound of the formula where the N0 group can be positioned anywhere in the benzene ring, can be reacted in dimethyl formamide with an alkali metal salt of a dihydric phenol of the general formula,
  • R is a divalent aromatic radical and Alk is an alkali metal ion.
  • Alk is an alkali metal ion.
  • alkali metal salts of the above described dihydric phenols are sodium and potassium salts of the following dihydric phenols,
  • organic diamines of Formula 2 are for example,
  • 4,4-diarninodiphenyl sulfide 4,4'-diaminodiphenyl sulfone; 4,4-diaminodiphenyl ether; 1,5-diaminonaphthalene; 3,3'-dimethylbenzidine; 3,3'-dimethoxybenzidine; 2,4-bis(/8-amino-t-butyl) toluene;
  • a mixture of the arcmatic bis(etheranhydride) and the organic diamine is heated under an inert atmosphere, such as a nitrogen atmosphere to form a homogenous melt and the water as it is formed is removed therefrom.
  • the temperature of the melt is maintained above the glass transition temperature of the resulting polyetherimide, but below a temperature of about 400 C.
  • the melt polymerization is conducted at a temperature of about between 250 C. to 300 C.
  • the polymerization is facilitated by purging the melt with an inert gas such as nitrogen. It also has been found expedient to employ reduced pressure at the final stage of the polymerization to facilitate removal of Water. Stirring of the mixture can be employed. The course of the reaction can be readily followed by the change in melt viscosity of the mixture.
  • Polyetherimide having from 2 to 500 and preferably to 50 average repeating units can be formed. These polymers can be blended with various fillers such as silica fillers, glass fibers, carbon whiskers, perlite, etc. The resulting filled compositions can have a proportion of from about 1 parts to 70 parts of filler per hundred parts of polyetherimide.
  • the blending of the filler with the polyetherimide can be achieved by adding the filler prior to forming the melt or directly to the melt. Stirring can be effected with a standard agitating means to facilitate blending the ingredients.
  • EXAMPLE 1 A mixture of 2,2 bis [4-(2,3-dicarboxyphenoxy)phenyl] propane dianhydride (3.0000 parts) and 4,4'-methylenedianiline (1.1418 parts) was heated to 290 C. for one half hour under nitrogen, and for one and one quarter hour in vacuo. The yield of the polymer was 2.0 parts. The intrinsic viscosity of the polymer in dimethylformamide was .46 dl./g. The elemental analysis found was: C, 77.8%; H, 4.5% and N, 4.1%. Calculated for (C H N O is: C, 77.4%; H, 4.4% and N, 4.1%. The infrared spectrum; k 1770, 1714, 1352, 1274 and 1239 cm.- Based on method of preparation, elemental analysis and spectral data, the product was a polyetherimide.
  • the above polyetherirnide is molded at 275 C. and a pressure of 5000-10,000 p.s.i. to a finished part.
  • the molded part forms an exact reproduction of the mold.
  • EXAMPLE 2 A mixture of 2,2-bis[4-(3,4-dicarboxyphenoxy)phenyl] propane dianhydride (3.0000 parts) and 4,4'-diaminodiphenyl ether (1.1520 parts) was heated at 300 C. with stirring for one-half hour under nitrogen, and for one and one-quarter hours in vacuo. The yield of the polymer was 2.68 parts. The intrinsic viscosity in dimethylacetamide was 1.00 dl./ g. The infrared spectrum was taken of a clear flexible film cast from a chloroform solution: A 1767, 1712, 1372, 1275, 1244 and 1217 cmr The thermal decomposition temperature of the polymer was 510 C. in introgen, and 410 C. in air as determined by thermal gravimetric analysis.
  • EXAMPLE 3 A mixture of 2,2-'bis[4-(3,4-dicarboxyphenoxy)phenyl] propane dianhydride (3.0000 parts), and, 4,4'-methylenedianiline (1.1418 parts) was heated at 290 C. for onehalf hour under nitrogen and one and one-quarter hours under vacuum. The yield of the amber glassy polymer was 4.0 parts. The intrinsic viscosity of the polymer was .65 dl./ g. in dimethylformamide. The thermal decomposition temperature of the polymer was 450 C. in nitrogen and 420 C. in air as determined by thermal gralvimetric analysis. A tough flexible tfilm was cast from a chloroform solution.
  • the polymer was a polyetherimide.
  • EXAMPLIE 5 A mixture of 4,4-diaminodiphenyl ether (1.2152 parts) and 4,4'-bis(2,3-dicarboxyphenoxy)diphenyl ether dianhydride (3.0000 parts) was heated to 290 C. under nitro gen with stirring. The yield of the tough glassy polymer was 2.8 parts. The intrinsic viscosity of the polymer was .53 dL/g. in chloroform. The elemental analysis found: C, 72.4%; H, 3.4% calculated for (C I-I -N O is C, 72.7%; H, 3.5% The thermal decomposition temperature was 480 C. in air is determined by thermo-gravimetric analysis.
  • EXAMPLE 6 A mixture of 4,4'-bis(3,4-dicarboxyphenoxy)diphenyl ether dianhydride (3.5228 parts) and hexamethylenediamine (.8529 part) was heated to 290 C. for one hour with stirring under nitrogen. The yield of the tough amber polymer was 3.0 parts. The intrinsic viscosity in chloroform was .48 dl./g. The elemental analysis. found was: C, 71.6%; H, 4.9% and N, 4.7%. Calculated for (C H N O is C, 70.8%; H, 4.97%; and N, 4.9%. The thermal decomposition temperature was 440 C. in nitrogen and 420 C. in air as determined by thermal gravimetric analysis.
  • EXAMPLE 7 A mixture of 1,4-bis(2,3-dicarboxyphenoxy)benzene dianhydride (2.5000 parts) and 4,4-methylenedianiline (1.2320 parts) was heated to 290 C. under nitrogen, with stirring for 1 hour. The yield of the polymer was 2.67 parts. The intrinsic viscosity in meta-cresol was 0.45 dL/g. The elemental analysis: C, 74.6%; H, 2.8%. Calculated for (CgzHmNzOg) is C, H, 2.9%. The infrared spectrum was taken from a tough flexible film cast from meta-cresol: A 1772, 1715, 1378, 1249 and 1885 MIL-1. The thermal decomposition temperature was 480 C. nitrogen and 480 C. in air as determined by thermal gravimetric analysis.
  • EXAMPLE 8 A mixture of 4,4'-bis(3,4 dicarboxyphenoxy)diphenylsulfide dianhydride (2.5571 parts) and bis-(4-aminobutyl)-tetramethyldisiloxane (1.4259 parts) were heated under nitrogen with stirring to 260 C. The yield of the polymer was 3.0 parts. The intrinsic viscosity in chloroform was 0.55 dL/g. The infrared spectrum was taken from a tough flexible film cast from chloroformi A 1762, 1702, 1440, 1390, 1230 and 1164- cm. The thermal decomposition temperature of the polymer was 450 C. in nitrogen and 410 C. in air as determined by thermal gravimetric analysis.
  • the intrinsic viscosity of the polymer was 4.6 dl./ g. in dimethylformamide.
  • the elemental analysis found was:
  • EXAMPLE 10 A mixture of 2,2-bis[4-(3,4-dicarboxyphenoxy)phenyl] propane dianhydride (50.0000 parts) and 4,4'-methylenedianiline (18.6722 parts) was heated to 270 C. under nitrogen with stirring for one and one-half hours. The intrinsicviscosity in dimethylformamide was .52 dl./g. The polymer was extruded at 275 C. by use of a screw extruder. Molded samples were made of the extruded material. The molded samples had a tensile strength of 11,300 p.s.i. and the elongation was 6.7%.
  • the infrared spectrum A 1768, 1700, 1360, 1250, 1078 cmr
  • the intrinsic viscosity 0415 the polymer in chloroform was 0.37 dl./g.
  • the thermal decomposition temperature of the polymer was 430 C. in nitrogen and 390 C. in air as determined by thermal gravimetric analysis.
  • EXAMPLE 13 A mixture of 2,2-bis[4-(2,3-dicarboxyphenoxy)]propane dianhydride (8.099 parts) and 2,4-toluenediamine (1.8628 parts) was heated under nitrogen at 240 C. for 15 minutes. The melt was further heated at 275 under vacuum for 0.5 hour. The polymer melt was cooled, dissolved in about 100 parts of chloroform. The solution was poured in methanol to yield 8.80 parts of polymer.
  • EXAMPLE 14 A mixture of 2,2-bis[4-(2,3-dicarboxyphenoxy)phenyl] propane dianhydride (6.690 parts) and hexamethylenediamine (1.494 parts) was heated at 225 for 20 minutes at 245 for 40 minutes and then at 245 under vacuum for minutes. On cooling, amber colored, tough polymer was obtained in 93.4% yield. 0n the basis of the method of preparation, the polymer possesses the chemical constituent of caqHazNgogl Analysis found C, 74.7 and H, 5.5; calc. C, 74.0 and H, 5.4.
  • the polymer was a polyetherimide. It is molded to a finished part in accordance with the procedure of Example 1.
  • a method for making polyetherimide which comprises eiiecting the removal of water of reaction at temperatures of up to 400 C. by using either stirring an inert gas purge or reduced pressure from the melt of a mixture containing as essential ingredients aromatic bis- (etheranhydride) of the formula and organic diamine of the formula,

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  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
  • Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
US00319372A 1972-12-29 1972-12-29 Method for making polyetherimides Expired - Lifetime US3803085A (en)

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Application Number Priority Date Filing Date Title
US00319372A US3803085A (en) 1972-12-29 1972-12-29 Method for making polyetherimides
US00372743A US3833546A (en) 1972-12-29 1973-06-22 Method for making polyetherimides
DE2363784A DE2363784C2 (de) 1972-12-29 1973-12-21 Verfahren zum Herstellen von Polyätherimiden
GB5935673A GB1463299A (en) 1972-12-29 1973-12-21 Method for making polyetherimides
CA188,947A CA1013492A (en) 1972-12-29 1973-12-27 Method for making polyetherimides
JP744918A JPS5720967B2 (enrdf_load_stackoverflow) 1972-12-29 1973-12-27
IT32186/73A IT1002289B (it) 1972-12-29 1973-12-27 Metodo per fare polieterimmidi
FR7347097A FR2225466B1 (enrdf_load_stackoverflow) 1972-12-29 1973-12-28
US05/439,866 US3989670A (en) 1972-12-29 1974-02-06 Method for making polyetherimides
FR7428600A FR2225470B1 (enrdf_load_stackoverflow) 1972-12-29 1974-08-20

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US05/549,469 Continuation-In-Part US4011198A (en) 1974-04-08 1975-02-13 Method for making polyetherimides

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JP (1) JPS5720967B2 (enrdf_load_stackoverflow)
DE (1) DE2363784C2 (enrdf_load_stackoverflow)
FR (2) FR2225466B1 (enrdf_load_stackoverflow)
GB (1) GB1463299A (enrdf_load_stackoverflow)
IT (1) IT1002289B (enrdf_load_stackoverflow)

Cited By (124)

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US6476182B1 (en) 2000-12-21 2002-11-05 E. I. Du Pont De Nemours And Company Melt-processible, thermoplastic random copolyimides having recoverable crystallinity and associated processes
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IT1002289B (it) 1976-05-20
FR2225470B1 (enrdf_load_stackoverflow) 1977-11-04
DE2363784C2 (de) 1985-08-29
DE2363784A1 (de) 1974-07-04
FR2225466A1 (enrdf_load_stackoverflow) 1974-11-08
FR2225470A1 (enrdf_load_stackoverflow) 1974-11-08

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